Why incumbents struggle to fix CPQ

Glean started as a Kleiner Perkins incubation and is now a $7B, $200m ARR Enterprise AI leader. Now KP has tapped its own podcaster to lead it’s next big swing.

From building go-to-market the hard way in startups (and scaling Palo Alto Networks’ public cloud business) to joining Kleiner Perkins to help technical founders turn product edge into repeatable revenue, Joubin Mirzadegan has spent the last decade obsessing over one thing: distribution and how ideas actually spread, sell, and compound. That obsession took him from launching the CRO-only podcast Grit (https://www.youtube.com/playlist?list=PLRiWZFltuYPF8A6UGm74K2q29UwU-Kk9k) as a hiring wedge, to working alongside breakout companies like Glean and Windsurf, to now incubating Roadrunner which is an AI-native rethink of CPQ and quoting workflows as pricing models collapse from “seats” into consumption, bundles, renewals, and SKU sprawl.

We sat down with Joubin to dig into the real mechanics of making conversations feel human (rolling early, never sending questions, temperature + lighting hacks), what Windsurf got right about “Google-class product and Salesforce-class distribution,” how to hire early sales leaders without getting fooled by shiny logos, why CPQ is quietly breaking the back of modern revenue teams, and his thesis for his new company and KP incubation Roadrunner (https://www.roadrunner.ai/): rebuild the data model from the ground up, co-develop with the hairiest design partners, and eventually use LLMs to recommend deal structures the way the best reps do without the Slack-channel chaos of deal desk.

We discuss:

• How to make guests instantly comfortable: rolling early, no “are you ready?”, temperature, lighting, and room dynamics

• Why Joubin refuses to send questions in advance (and when you might have to anyway)

• The origin of the CRO-only podcast: using media as a hiring wedge and relationship engine

• The “commit to 100 episodes” mindset: why most shows die before they find their voice

• Founder vs exec interviews: why CEOs can speak more freely (and what it unlocks in conversation)

• What Glean taught him about enterprise AI: permissions, trust, and overcoming “category is dead” skepticism

• Design partners as the real unlock: why early believers matter and how co-development actually works

• Windsurf’s breakout: what it means to be serious about “Google-class product + Salesforce-class distribution”

• Why technical founders struggle with GTM and how KP built a team around sales, customer access, and demand gen

• Hiring early sales leaders: anti-patterns (logos), what to screen for (motivation), and why stage-fit is everything

• The CPQ problem & Roadrunner’s thesis: rebuilding CPQ/quoting from the data model up for modern complexity

• How “rules + SKUs + approvals” create a brittle graph and what it takes to model it without tipping over

• The two-year window: incumbents rebuilding slowly vs startups out-sprinting with AI-native architecture

• Where AI actually helps: quote generation, policy enforcement, approval routing, and deal recommendation loops

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Joubin

• X: https://x.com/Joubinmir

• LinkedIn: https://www.linkedin.com/in/joubin-mirzadegan-66186854/

Where to find Latent Space

• X: https://x.com/latentspacepod

• Substack: https://www.latent.space/

Chapters

• 00:00:00 Introduction and the Zuck Interview Experience
• 00:03:26 The Genesis of the Grit Podcast: Hiring CROs Through Content
• 00:13:20 Podcast Philosophy: Creating Authentic Conversations
• 00:15:44 Working with Arvind at Glean: The Enterprise Search Breakthrough
• 00:26:20 Windsurf's Sales Machine: Google-Class Product Meets Salesforce-Class Distribution
• 00:30:28 Hiring Sales Leaders: Anti-Patterns and First Principles
• 00:39:02 The CPQ Problem: Why Salesforce and Legacy Tools Are Breaking
• 00:43:40 Introducing Roadrunner: Solving Enterprise Pricing with AI
• 00:49:19 Building Roadrunner: Team, Design Partners, and Data Model Challenges
• 00:59:35 High Performance Philosophy: Working Out Every Day and Reducing Friction
• 01:06:28 Defining Grit: Passion Plus Perseverance